GUAIAZULENE

First approved in 2018

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18
Molecular Weight	198.3034
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1

InChI

InChIKey=FWKQNCXZGNBPFD-UHFFFAOYSA-N

InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

HIDE SMILES / InChI

Description
Sources: http://www.cosmeticsinfo.org/ingredient/guaiazulene-0
Curator's Comment: description was created based on several sources, including: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=73.2180 https://www.ncbi.nlm.nih.gov/pubmed/26401381

Guaiazulene is a blue compound. It is a derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil. Guaiazulene is an U.S. FDA-approved cosmetic color additive. Guaiazulene is used in the formulation of bath products, cleansing products, depilatories, hair bleaches, hair conditioners, hair dyes and colors, hair straighteners, permanent waves, skin care products and skin fresheners. Guaiazulene has antioxidant, antifungal, antimicrobial, anti-inflammatory, anti-spasmodic, anti-ulcer, antitumoral activities and relaxant properties. Common side effects are: iarrhea, constipation, etc.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
Cytochrome P450 2B6 19 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9112807	Inhibitor 8297
lipid oxidation 20 Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9306266	Inhibitor 8297	9.8 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 67 Sources: http://www.120ty.net/bencandy.php?fid=141&id=43550	Primary	Approved 8429	ANZUWEI Approved Use It is usually used in the treatment of gastric ulcer. Launch Date 1976
Gastritis 45 Sources: http://www.120ty.net/bencandy.php?fid=141&id=43550	Primary	Approved 8429	ANZUWEI Approved Use It is usually used in the treatment of gastritis. Launch Date 1976
Corneal burns 1 Sources: https://pribalovy-letak.info/ophthalmo-azulen	Primary	Approved 8429	Ophthalmo-Azulen Approved Use It has been used for ocular burns and corneal burns.
Eyelids, conjunctiva and cornea injuries 1 Sources: https://pribalovy-letak.info/ophthalmo-azulen	Primary	Approved 8429	Ophthalmo-Azulen Approved Use Ophthalmo-Azulen is used in adults and children for eyelids, conjunctiva and cornea injure treatment, to accelerate the healing process after removing foreign bodies from the cornea.

PubMed

Title	Date	PubMed
[Use of garmastan in the prophylaxis and therapy of sore nipples of the breast].	2001	11803878
Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.	2002 Jul	12130848
Intraindividual comparison of two different skin care conceptions in patients undergoing radiotherapy of the head-and-neck region. Creme or powder?	2002 Jun	12122788
Determination of the temperature dependence of water solubilities of polycyclic aromatic hydrocarbons by a generator column-on-line solid-phase extraction-liquid chromatographic method.	2002 Jun	12108700
Synthesis and antioxidant activity of 3-substituted guaiazulene derivatives.	2002 Jun	12049221
Solvatochromism, halochromism, and preferential solvation of new dipolar guaiazulenyl 1,4-benzoquinone methides.	2003 Apr 21	12929672
Calenzanane sesquiterpenes from the red seaweed Laurencia microcladia from the Bay of Calenzana, Elba Island: acid-catalyzed stereospecific conversion of calenzanol into indene- and guaiazulene-type sesquiterpenes.	2003 Dec 5	14673847
Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.	2003 May	12802730
Moist skin care can diminish acute radiation-induced skin toxicity.	2003 Oct	14566480
Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene.	2003 Sep 29	14563527
Temperature dependence of the infinite dilution activity coefficient and Henry's law constant of polycyclic aromatic hydrocarbons in water.	2004 Aug	15212897
Reaction of a terminal phosphinidene complex with azulenes: eta1-complexes, C--H bond insertions, and 1,4-adducts.	2004 Jun 7	15195304
A convenient synthetic route to benz[cd]azulenes: versatile ligands with the potential to bind metals in an eta5, eta6, or eta7 fashion.	2004 Oct 25	15378728
Comparative analysis of the oil and supercritical CO(2) extract of Artemisia arborescens L. and Helichrysum splendidum (Thunb.) Less.	2006 May 10	16644539
Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines.	2008 Aug 22	18706312
Guaiazulene in health care products: determination by GC-MS and HPLC-DAD and photostability test.	2008 Aug 5	18395389
Enhancement of Escherichia coli and Staphylococcus aureus antibiotic susceptibility using sesquiterpenoids.	2008 Nov	18991747
Study on the photostability of guaiazulene by high-performance liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry.	2008 Sep	18680092
Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.	2009 Dec 3	19904921
Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption.	2009 Mar 9	19216881
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.	2010 May 15	20385420
Cytotoxic activity of guaiazulene on gingival fibroblasts and the influence of light exposure on guaiazulene-induced cell death.	2011 Feb	20854889

Patents

Sample Use Guides

In Vivo Use Guide

Take 1 tablet (2 mg of the active ingredient) at a time, three times daily, before meals.

Route of Administration: Other

In Vitro Use Guide

Guaiazulene caused statistically important increases in total oxidative stress levels at concentrations higher than 100 µg/mL in rat neuron cell line.

Name

Type

Language

GUAIAZULENE

Official Name

English

7-ISOPROPYL-1,4-DIMETHYLAZULENE

Systematic Name

English

1,4-DIMETHYL-7-ISOPROPYLAZULENE

Systematic Name

English

KESSAZULEN

Common Name

English

GUAIAZULENE (CONSTITUENT OF CHAMOMILE) [DSC]

Common Name

English

GUAIAZULENE [MART.]

Common Name

English

UROAZULEN

Common Name

English

S-GUAIAZULENE

Common Name

English

NSC-4714

Code

English

VAUMIGAN

Common Name

English

Guaiazulene [WHO-DD]

Common Name

English

GUAIAZULENE [MI]

Common Name

English

VETIVAZULEN

Common Name

English

GUAIAZULEN

Common Name

English

PURAZULEN

Common Name

English

SILAZULON

Common Name

English

1,4-DIMETHYL-7-ISOPROPYL-AZULENE

Systematic Name

English

GUAIAZULENE [INCI]

Common Name

English

AZULENE, 1,4-DIMETHYL-7-(1-METHYLETHYL)-

Systematic Name

English

1,4-DIMETHYL-7-ISOPROPYLAZULENE [JAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01XA01